Dear was a student at VMI at the beginning of the war. He matriculated at Randolph-Macon in the fall of 1862, under the military curriculum patterned after VMI that was taught by a VMI graduate, James E. Blankenship. He joined Mosby's Rangers, Co. D of the 43rd VA Cavalry, in the early months of 1863. He participated in numerous raids and was alleged to have been wounded at lest 12 times. He was paroled in Winchester, VA, on May 17, 1865.
After the war, he ran an inn in Washington, VA, and eventually went to work for the IRS. He died January 5, 1929 and is buried in Washington Cemetery in Washington, VA
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